Regiocontrolled Synthesis of 1,2-Di(organo)fullerenes via Copper-Assisted 1,4-Aryl Migration from Silicon to Carbon

A concise and efficient way to generate fullerene cationic species through the oxidation of a fullerene radical or a fullerene anion with a Cu(II) salt has been developed. It was demonstrated that the cationic fullerene is useful for functionalization of fullerene, in particular, for the synthesis of noncyclic 1,2-di(organo)[60]fullerene derivatives that can be selectively prepared through intramolecular 1,4-aryl migration of an aryl group from a silicon atom to the fullerene core.